Organometallics
Organometallics
5 years ago

Ring Opening of Epoxides Induced by Pentaphenylborole

Ring Opening of Epoxides Induced by Pentaphenylborole
Sam Yruegas, Jason L. Dutton, Caleb D. Martin, Charles Wilson
The unsaturated antiaromatic BC4 heterocycle pentaphenylborole has been shown to have diverse reactivity with a variety of substrates, including the insertion of polar functional groups into the ring as a route to conjugated boracycles. This work investigates the reactivity of a selection of epoxides with pentaphenylborole, both computationally and experimentally, revealing that the substitution is highly influential on the reaction outcome. Specifically, isobutylene oxide results in protodeborylation to a borabutadiene chain attributed to the acidic β-hydrogen atoms, 1,1-diphenylethylene oxide inserts the C2O unit to furnish a BOC6 heterocycle, and cyclohexene oxide inserts two epoxides to form an unusual BC8O2 ring. The last two species represent rare boron-containing rings of eight atoms or greater, with the 11-membered species being only the second reported and the first crystallographically characterized.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00152

DOI: 10.1021/acs.organomet.7b00152

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.